10 celebs who've been engaged multiple times: From Jennifer Lopez to Johnny Depp

10 celebs who've been engaged multiple times: From Julia Roberts to Kim Kardashian

While many Hollywood celebrity marriages end in divorce, some celebrities never get past the engagement phase before separating. According to fairytales, a classic love narrative should culminate in a romantic date, a passionate proposal, and an idyllic wedding before the pair lives happily ever after. Sadly, Brad Pitt and Julia Roberts are examples of how unrealistic those ideals might be. See below for a list of 10 famous people who have gotten engaged three or more times.

1. Kaley Cuoco: 4 engagements

'Flight Attendant' actress Kaley Cuoco recently revealed that she and Tom Pelphrey are engaged, which marks Kaley's fourth engagement announcement. Kaley's first fiance was addiction doctor, Josh Resnik, who proposed to her in 2011 but they broke up in 2012 before they married. Tennis player Ryan Sweeting proposed to the 'Big Bang Theory' star in September 2013 and they were married from December 2013 to 2015. Equestrian Karl Cook proposed to her on her birthday in December 2017. They were married in 2018 but declared their divorce in 2021, per Hello! magazine.

2. Jennifer Lopez: 6 engagements

Waiter-turned-restaurateur Ojani Noa was Jennifer Lopez's first fiance with whom she married in 1997 but divorced less than a year later. The 'On The Floor' hitmaker later married backup dancer Cris Judd in 2001, but the couple separated after only nine months. Following their breakup, she became engaged to Ben Affleck; however, the pair called it quits shortly before her wedding. She moved on with Marc Anthony, with whom she quickly became engaged and married in 2004. Following their split in 2014, Alex Rodriguez proposed to Lopez in 2019 but the couple called it quits in 2021. Affleck and Lopez reignited their romance in 2022, almost 20 years after their initial engagement. The couple eventually got married in July 2022 but Lopez officially filed for divorce in 2024.

3. Brad Pitt: 4 engagements

Brad Pitt proposed to his girlfriend Jill Schoelen before becoming famous in Hollywood. However, she ended their relationship after Pitt left town to shoot a movie. He then proposed to actress Gwyneth Paltrow but parted ways in 1997. In 1999, Pitt later proposed to Jennifer Aniston and the two tied the knot in 2000. However, their five-year marriage came to an end in 2005. The 'Troy' actor reportedly fell in love with his second wife, Angelina Jolie, on the set of 'Mr. & Mrs. Smith' but they didn't get engaged until 2012. They got married in 2014 but she filed for divorce in 2016.

4. Elizabeth Taylor: 10 engagements

Elizabeth Taylor had eight marriages and 10 engagements! William Pawley Jr was Elizabeth's first fiance; Conrad Hilton Jr, who was also her first husband, was her second fiance. Actor Michael Wilding was the third fiance and second husband, and producer Mike Todd was the next, but their marriage ended tragically when he died in a plane crash. Elizabeth became close to Mike's friend Eddie Fisher after his death, and the two were married from 1959 until 1964. The 'Cleopatra' actress' most famous romance was arguably her two marriages to Richard Burton, which began in 1964 and 1974, respectively, and lasted less than a year in each case. She subsequently went on to infamously be engaged and married to politician John Warner and construction worker Larry Fortensky. Victor Luna and Dennis Stein, who both had their engagement rings accepted by Elizabeth but eventually called it quits, round out her final two engagements.

5. Julia Roberts: 4 engagements

Julia Roberts was engaged three times before she married her long-term partner Daniel Moder in 2002. The actress initially became engaged to her 'Steel Magnolias' co-star Dylan McDermott, and then to Kiefer Sutherland, with whom she broke up a few days before their scheduled 1991 wedding. Following that, she had a fast-paced affair with Lyle Lovett, which culminated in their 1993 small-town wedding in Indiana, after barely three weeks of dating. Their union ended in divorce in 1995, after just two years of marriage.

6. Paris Hilton: 4 engagements

Paris Hilton, who has never been married before, accepted her boyfriend Carter Reum's marriage proposal with joy in 2021. However, she has been engaged three times previously. Paris got engaged for the first time in 2003 to model Jason Shaw, but they broke up a few months later. Greek shipping heir Paris Latsis proposed to her two years later, but she called it off again a few months later. Actor Chris Zylka and Paris announced their engagement in January 2018, but they called it quits less than a year later. Paris knew her husband Carter for 15 years before their acquaintance blossomed into romance in 2019. In 2021, he proposed to her and they got married eight months later.

7. Kim Kardashian: 3 engagements

Kim Kardashian married producer Damon Thomas when she was 19 years old but the couple divorced in 2004. In May 2011, professional basketball player Kris Humphries proposed to Kim with a Lorraine Schwartz ring, less than a year after they first started dating. They got married in August, but she filed for divorce within 72 days. Kanye West went all out when he proposed to her in 2013 inside a San Francisco baseball stadium, giving her a 15-carat ring. They got married in Italy in 2014 but got divorced in 2022.

8. Kate Hudson: 3 engagements

Kate Hudson has received three stunning rings over the years, the first being from Chris Robinson. Kate began her whirlwind romance with Chris at the age of 20. Their seven-year marriage came to an end in 2007, and Kate later became engaged to Matt Bellamy in 2011. However, they parted ways in 2014 before Kate tied the knot. The 'How to Lose a Guy in 10 Days' star dated current fiance Danny Fujikawa for four years before he proposed in 2021. The two had been friends for 15 years before their romance began.

9. Drew Barrymore: 5 engagements

Drew Barrymore got engaged for the first time to Leland Hayward III at the tender age of 16, but the relationship was short-lived. Barrymore also had a brief relationship with actor Jamie Waters, but her third fiance, Jeremy Thomas, was the first to marry her. Barrymore wed Thomas in 1994 at the age of 19, and he was 31 years old, but they split within a month. Tom Green was Barrymore's fourth fiance and they got married in Malibu in 2001; however, the couple parted ways in 2002. Eventually, she married her ex-husband Will Kopelman in 2012. The couple had two children together before calling it quits in 2016.

10. Johnny Depp: 6 engagements

Although Johnny Depp has only been married twice, it is believed that he has been engaged six times. His two marriages were to Amber Heard, who divorced him in 2016 after less than a year of marriage; and Lori Anne Allison, who divorced him in 1985 after two years of marriage. Depp has also been engaged to Winona Ryder, Jennifer Grey, and Sherilyn Fenn, without ever walking down the aisle. Moreover, Depp was reportedly once engaged to Vanessa Paradis, his long-term girlfriend of 14 years and the mother of his children, however, none of them ever decided to tie the knot.